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内部酸化剤としてN-N結合を用いたロジウム (((III)) 触媒によるインドル合成

Baoqing Liu¹, Chao Song, Chao Sun

¹Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, Nanjing University , Nanjing 210093, China.

Journal of the American Chemical Society

|October 10, 2013

まとめ

この研究では,N-ニトロソアニリンとアルキンからインドールを合成するためのRh (III) 触媒反応を導入しています. この新しい方法は,効率的な触媒の周回とC-H活性化のための酸化剤として内部N-N結合を使用しています.

科学分野:

有機化学オーガニック・ケミストリー
カタリシスカタリシスカタリシス
合成方法論合成方法論

背景:

インドール・スキャフォールは,医薬品や天然製品に多く見られます.
代替インドルへの効率的で汎用的な合成経路は,非常に求められています.
以前の方法は,しばしば厳しい条件を必要とし,または幅広い機能群の許容性が欠如しています.

研究の目的:

インドール合成のための新しいRh(III) 触媒化されたサイクライゼーションの開発.
C-H活性化を利用したリドックス中性多様体を確立する.
新しいプロトコルの汎用性と機能グループ耐性を実証するために.

主な方法:

N-ニトロソアニリンとアルキンの間のRh(III) 触媒サイクリング反応.
N-ニトロソアニリンの内部N-N結合を,固有の内部酸化剤として利用する.
触媒サイクルにおける重要なステップとして,C-H活性化を使用します.

主要な成果:

インドールの簡素化された合成が達成された.
分子間レドックス中性多様体を示した.
酸性および塩基性条件の両方との互換性を示しました.
幅広い補助機能群に対する許容性を示し,プログラム可能な置換を可能にします.

結論:

開発されたRh(III) 触媒プロトコルは,多様なインドル誘導体への効率的で汎用的な経路を提供します.
内部のN-N結合は,触媒の回転のためのユニークな反応ハンドルとして機能します.
C-Hの活性化は売上を制限するステップとして識別され,メカニズム的な洞察を提供します.

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